287100-00-9Relevant academic research and scientific papers
The absolute configuration and asymmetric total synthesis of the CP molecules (CP-263,114 and CP-225,917, phomoidrides B and A)
Nicolaou,Jung, Jae-Kyu,Yoon, Won Hyung,He, Yun,Zhong, Yong-Li,Baran, Phil S.
, p. 1829 - 1832 (2007/10/03)
An intramolecular Diels-Alder reaction with substrate-based control of the diastereoselectivity allowed the asymmetric synthesis of the core of the CP compounds 2. The specially designed triene 1, which contains a bulky chiral moiety capable of influencing the facial selectivity of the cycloaddition, was converted into the major diastereomer 2 with 70% de (see scheme). The elucidation of the absolute configuration of this precursor allowed for the synthesis of the enantiomerically pure forms of the bioactive CP molecules and now sets the stage for the design of simpler, optically active analogues.
